N-(3-Methyl­phen­yl)methane­sulfonamide

The conformation of the N—H bond in the structure of the title compound (3MPMSA), C₈H₁₁NO₂S, is anti to the meta-methyl substituent, similar to that observed in the corresponding meta-nitro-substituted sulfonanilide (3NPMSA). The bond parameters in the three compounds, PMSA, 3MPMSA and 3NPMSA, are similar except in the S—N—C angle and in the S—N—C—C torsion angles. The mol­ecules are linked into chains in the direction of the c axis through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.048
• wR factor = 0.124
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.07
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.070
            Tmax scaled      0.918 Tmin scaled      0.666

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The stereochemistry of biologically important alkyl sulfonanilides is of interest in explaining their biological activity. The biological activity may be due to N—H group. Therefore the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3-methylphenyl)-methanesulfonamde (3MPMSA) has been determined to explore the substituent effects on the structures of anilides and sulfonanilides (Gowda et al., 2000, 2007, 2007a,b). The conformation of the N—H bond in the structure of 3MPMSA, is anti to the meta-methyl substituent (Fig.1), similar to that observed in the corresponding meta- nitro substituted sulfonanilide (3NPMSA)(Gowda et al., 2007b). The bond parameters in the 3 compounds, PMSA (Klug, 1968), 3MPMSA and 3NPMSA are similar except in the S—N—C bond angle [120.0 (1)° (PMSA); 121.2 (2)° (3MPMSA); 126.3 (3)° (3NPMSA)] and in the S—N—C—C torsion angles [S2—N5—C6—C7 and S2—N5—C6—C11: 75.5 (2)° and -106.6 (2)° (PMSA); 68.1 (4)° and -114.3 (3)° (3MPMSA); 41.1 (3)°, -140.8 (2)° (3NPMSA)]. The molecules are linked in chains in the direction of c axis through N—H···O hydrogen bonds. (Table 1 and Fig. 2).

Related literature

For related literature, see: Gowda et al. (2007); Gowda et al. (2007a); Gowda et al. (2007b); Gowda et al. (2000); Jayalakshmi & Gowda (2004); Klug (1968).

S2. Experimental

The title compound was prepared according to the literature method (Jayalakshmi & Gowda, 2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Jayalakshmi & Gowda, 2004). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution.

S3. Refinement

Methyl groups were refined as riding with C—H = 0.96Å and U_iso(H) = 1.2 U_eq(C). The coordinates of the remaining H atoms were refined with U_iso(H) = 1.2 U_eq(C,N).

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The crystal packing of the title compound, viewed down the b axis.

N-(3-Methylphenyl)methanesulfonamide

Crystal data

C8H11NO2S	F(000) = 784
Mr = 185.24	Dx = 1.348 Mg m^−3
Orthorhombic, Pccn	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 25 reflections
a = 23.218 (2) Å	θ = 3.8–22.8°
b = 8.4933 (7) Å	µ = 2.84 mm^−1
c = 9.2561 (8) Å	T = 299 K
V = 1825.3 (3) Å^3	Laminar, colourless
Z = 8	0.25 × 0.10 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	975 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 66.8°, θmin = 3.8°
ω/2θ scans	h = −27→0
Absorption correction: psi-scan (North et al., 1968)	k = −10→2
Tmin = 0.623, Tmax = 0.859	l = −11→0
1875 measured reflections	3 standard reflections every 120 min
1618 independent reflections	intensity decay: 2.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
1618 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.36 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.49810 (16)	0.2700 (5)	0.0568 (4)	0.0565 (10)
H1A	0.5140	0.3265	0.1373	0.068*
H1B	0.4865	0.3432	−0.0166	0.068*
H1C	0.5267	0.1999	0.0183	0.068*
C6	0.37038 (14)	0.4150 (4)	0.1081 (4)	0.0370 (8)
C7	0.33344 (16)	0.3904 (5)	−0.0062 (4)	0.0435 (9)
H7	0.3240 (15)	0.295 (4)	−0.033 (4)	0.052*
C8	0.31135 (16)	0.5164 (5)	−0.0843 (4)	0.0492 (10)
C9	0.32608 (18)	0.6653 (6)	−0.0410 (5)	0.0575 (11)
H9	0.3117 (16)	0.744 (6)	−0.089 (5)	0.069*
C10	0.36123 (19)	0.6921 (5)	0.0767 (5)	0.0567 (12)
H10	0.3701 (16)	0.791 (5)	0.105 (5)	0.068*
C11	0.38420 (17)	0.5653 (5)	0.1511 (4)	0.0487 (10)
H11	0.4078 (16)	0.577 (5)	0.230 (4)	0.058*
C12	0.27302 (19)	0.4873 (6)	−0.2119 (5)	0.0807 (16)
H12A	0.2589	0.5860	−0.2480	0.097*
H12B	0.2411	0.4226	−0.1831	0.097*
H12C	0.2945	0.4348	−0.2863	0.097*
N5	0.39317 (13)	0.2824 (4)	0.1876 (3)	0.0431 (8)
H5N	0.4022 (15)	0.309 (4)	0.2740 (17)	0.052*
O3	0.41179 (11)	0.0963 (3)	−0.0128 (2)	0.0502 (7)
O4	0.45564 (12)	0.0557 (3)	0.2256 (3)	0.0597 (8)
S2	0.43830 (4)	0.16131 (9)	0.11400 (8)	0.0400 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.060 (2)	0.046 (2)	0.063 (2)	−0.005 (2)	−0.002 (2)	−0.004 (2)
C6	0.0430 (19)	0.0377 (17)	0.0302 (16)	0.0040 (16)	0.0050 (16)	0.0004 (18)
C7	0.048 (2)	0.043 (2)	0.0400 (19)	0.0059 (18)	−0.0015 (18)	−0.0052 (19)
C8	0.047 (2)	0.053 (2)	0.048 (2)	0.0124 (19)	−0.0021 (19)	0.005 (2)
C9	0.053 (3)	0.055 (3)	0.064 (3)	0.012 (2)	0.002 (2)	0.018 (3)
C10	0.052 (2)	0.037 (2)	0.081 (3)	−0.0026 (19)	0.007 (2)	0.000 (2)
C11	0.053 (2)	0.046 (2)	0.046 (2)	0.000 (2)	−0.0027 (19)	−0.003 (2)
C12	0.086 (3)	0.084 (4)	0.072 (3)	0.028 (3)	−0.034 (3)	−0.005 (3)
N5	0.0595 (19)	0.0441 (18)	0.0256 (14)	0.0099 (16)	−0.0017 (15)	0.0024 (14)
O3	0.0723 (17)	0.0407 (14)	0.0375 (13)	0.0003 (14)	−0.0112 (12)	−0.0093 (12)
O4	0.088 (2)	0.0473 (15)	0.0436 (14)	0.0134 (15)	−0.0116 (14)	0.0162 (13)
S2	0.0588 (5)	0.0311 (4)	0.0302 (4)	0.0028 (4)	−0.0063 (4)	0.0011 (4)

Geometric parameters (Å, º)

C1—S2	1.749 (4)	C9—H9	0.87 (4)
C1—H1A	0.9600	C10—C11	1.385 (5)
C1—H1B	0.9600	C10—H10	0.90 (4)
C1—H1C	0.9600	C11—H11	0.92 (4)
C6—C11	1.375 (5)	C12—H12A	0.9600
C6—C7	1.378 (5)	C12—H12B	0.9600
C6—N5	1.446 (4)	C12—H12C	0.9600
C7—C8	1.389 (5)	N5—S2	1.618 (3)
C7—H7	0.87 (4)	N5—H5N	0.856 (10)
C8—C9	1.370 (6)	O3—S2	1.436 (2)
C8—C12	1.500 (5)	O4—S2	1.426 (2)
C9—C10	1.380 (6)
S2—C1—H1A	109.5	C11—C10—H10	119 (3)
S2—C1—H1B	109.5	C6—C11—C10	119.2 (4)
H1A—C1—H1B	109.5	C6—C11—H11	118 (3)
S2—C1—H1C	109.5	C10—C11—H11	123 (3)
H1A—C1—H1C	109.5	C8—C12—H12A	109.5
H1B—C1—H1C	109.5	C8—C12—H12B	109.5
C11—C6—C7	120.6 (3)	H12A—C12—H12B	109.5
C11—C6—N5	119.4 (3)	C8—C12—H12C	109.5
C7—C6—N5	120.0 (3)	H12A—C12—H12C	109.5
C6—C7—C8	120.8 (4)	H12B—C12—H12C	109.5
C6—C7—H7	121 (3)	C6—N5—S2	121.2 (2)
C8—C7—H7	118 (3)	C6—N5—H5N	111 (2)
C9—C8—C7	117.8 (4)	S2—N5—H5N	114 (2)
C9—C8—C12	122.0 (4)	O4—S2—O3	118.09 (16)
C7—C8—C12	120.2 (4)	O4—S2—N5	106.12 (15)
C8—C9—C10	122.0 (4)	O3—S2—N5	108.12 (16)
C8—C9—H9	118 (3)	O4—S2—C1	109.09 (18)
C10—C9—H9	120 (3)	O3—S2—C1	107.21 (17)
C9—C10—C11	119.5 (4)	N5—S2—C1	107.82 (18)
C9—C10—H10	121 (3)
C11—C6—C7—C8	2.8 (6)	N5—C6—C11—C10	−178.5 (4)
N5—C6—C7—C8	−179.7 (3)	C9—C10—C11—C6	−1.5 (6)
C6—C7—C8—C9	−2.0 (6)	C11—C6—N5—S2	−114.3 (3)
C6—C7—C8—C12	177.6 (4)	C7—C6—N5—S2	68.2 (4)
C7—C8—C9—C10	−0.6 (6)	C6—N5—S2—O4	174.6 (3)
C12—C8—C9—C10	179.8 (4)	C6—N5—S2—O3	−57.7 (3)
C8—C9—C10—C11	2.3 (7)	C6—N5—S2—C1	57.9 (3)
C7—C6—C11—C10	−1.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O3^i	0.86 (1)	2.14 (1)	2.990 (4)	169 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.